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Nichols DE, Monte A, Huang X, Marona-Lewicka D. 
“Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent”. 
Behav Brain Res. 1996 Dec;73(1-2):117-9.
Studies of the affinities for serotonin 5-HT2A and 5-HT1A receptor subtypes of lysergic acid amides prepared from chiral 2-aminoalkanes showed a stereoselective preference at both receptor types for the amides with alkyl groups containing the R configuration. The 5-HT2A receptor was less tolerant of long alkyl groups than was the 5-HT1A subtype. In vivo assays in rats trained to discriminate LSD from saline also showed that amides with alkyl groups having the R configuration were most potent.
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